Water → 4-(6-Methyl-pyridin-2-yloxymethyl)-benzaldehyde

HRID 1690911

반응식

HRID 1690911 반응식
Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=2)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:24]=[O:25].O>O1CCCC1.C(OCC)(=O)C>[CH3:14][C:10]1[N:9]=[C:8]([O:7][CH2:6][C:5]2[CH:15]=[CH:16][C:2]([CH:24]=[O:25])=[CH:3][CH:4]=2)[CH:13]=[CH:12][CH:11]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 592554782-(4-Bromo-benzyloxy)-6-methyl-pyridineHCID 178418339Butyllithium

생성물 1

HCID 592551484-(6-Methyl-pyridin-2-yloxymethyl)-benzaldehyde수율 70.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 2-(4-bromo-benzyloxy)-6-methyl-pyridine (7.30 g, 26.2 mmol) described in Manufacturing Example 3-1-1 in anhydrous tetrahydrofuran (200 mL) was added dropwise n-butyl lithium (2.67 M n-hexane solution, 11.8 mL, 31.4 mmol) on a dry ice-ethanol bath (−78° C.), which was stirred for 30 minutes at −78° C. N,N-dimethylformamide (4.04 mL, 52.4 mmol) was added to this mixture at −78° C., and stirred for 5 minutes. Water and ethyl acetate were added to the reaction mixture, which was stirred for 10 minutes at room temperature, and the organic layer was then separated. This organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3) to obtain the title compound (4.19 g, 70%).

후처리

  1. stirringstirred for 5 minutes
  2. stirringwas stirred for 10 minutes at room temperature
  3. customthe organic layer was then separated
  4. washThis organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3)

출처 및 근거

ORD 기록
ord-81f82948a8e0457896e24dc82b19a8a8
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153662B2

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